CA2874980A1 - A method of improving a process for the selective absorption of hydrogen sulfide - Google Patents
A method of improving a process for the selective absorption of hydrogen sulfide Download PDFInfo
- Publication number
- CA2874980A1 CA2874980A1 CA 2874980 CA2874980A CA2874980A1 CA 2874980 A1 CA2874980 A1 CA 2874980A1 CA 2874980 CA2874980 CA 2874980 CA 2874980 A CA2874980 A CA 2874980A CA 2874980 A1 CA2874980 A1 CA 2874980A1
- Authority
- CA
- Canada
- Prior art keywords
- sterically hindered
- absorbent composition
- range
- amine
- hindered amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 138
- 229910000037 hydrogen sulfide Inorganic materials 0.000 title claims abstract description 136
- 238000000034 method Methods 0.000 title claims abstract description 76
- 238000010521 absorption reaction Methods 0.000 title abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 247
- 150000001412 amines Chemical class 0.000 claims abstract description 163
- 239000002250 absorbent Substances 0.000 claims abstract description 128
- 230000002745 absorbent Effects 0.000 claims abstract description 128
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 114
- 239000007789 gas Substances 0.000 claims abstract description 104
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 57
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 46
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 44
- 238000005576 amination reaction Methods 0.000 claims abstract description 44
- 239000006184 cosolvent Substances 0.000 claims abstract description 35
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 28
- -1 sulfone compound Chemical class 0.000 claims abstract description 27
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 17
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003125 aqueous solvent Substances 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 22
- 150000003457 sulfones Chemical class 0.000 claims description 21
- 230000001172 regenerating effect Effects 0.000 claims description 7
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 239000008246 gaseous mixture Substances 0.000 abstract description 9
- 239000000243 solution Substances 0.000 description 40
- 239000007788 liquid Substances 0.000 description 24
- 238000011069 regeneration method Methods 0.000 description 21
- 238000005191 phase separation Methods 0.000 description 19
- 230000008929 regeneration Effects 0.000 description 19
- 239000002253 acid Substances 0.000 description 17
- 239000007791 liquid phase Substances 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 15
- 239000006096 absorbing agent Substances 0.000 description 14
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- 230000002378 acidificating effect Effects 0.000 description 12
- 238000004448 titration Methods 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000011651 chromium Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000567 combustion gas Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YDJTVHXQNJVWPL-UHFFFAOYSA-N thiolane 1,1-dioxide;hydrate Chemical compound O.O=S1(=O)CCCC1 YDJTVHXQNJVWPL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- HLAOLWFKQBAKSM-UHFFFAOYSA-N n-[2-[1-[2-(tert-butylamino)ethoxy]ethoxy]ethyl]-2-methylpropan-2-amine Chemical compound CC(C)(C)NCCOC(C)OCCNC(C)(C)C HLAOLWFKQBAKSM-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
- B01D53/1468—Removing hydrogen sulfide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1425—Regeneration of liquid absorbents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/02—Preparation of sulfur; Purification
- C01B17/04—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides
- C01B17/0404—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides by processes comprising a dry catalytic conversion of hydrogen sulfide-containing gases, e.g. the Claus process
- C01B17/0408—Pretreatment of the hydrogen sulfide containing gases
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/02—Preparation of sulfur; Purification
- C01B17/04—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides
- C01B17/0404—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides by processes comprising a dry catalytic conversion of hydrogen sulfide-containing gases, e.g. the Claus process
- C01B17/0456—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides by processes comprising a dry catalytic conversion of hydrogen sulfide-containing gases, e.g. the Claus process the hydrogen sulfide-containing gas being a Claus process tail gas
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/16—Hydrogen sulfides
- C01B17/167—Separation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/202—Alcohols or their derivatives
- B01D2252/2023—Glycols, diols or their derivatives
- B01D2252/2026—Polyethylene glycol, ethers or esters thereof, e.g. Selexol
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20405—Monoamines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/2041—Diamines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/20478—Alkanolamines
- B01D2252/20484—Alkanolamines with one hydroxyl group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/205—Other organic compounds not covered by B01D2252/00 - B01D2252/20494
- B01D2252/2056—Sulfur compounds, e.g. Sulfolane, thiols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/30—Sulfur compounds
- B01D2257/304—Hydrogen sulfide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/46—Removing components of defined structure
- B01D53/48—Sulfur compounds
- B01D53/52—Hydrogen sulfide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/34—Chemical or biological purification of waste gases
- B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
- B01D53/77—Liquid phase processes
- B01D53/78—Liquid phase processes with gas-liquid contact
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Environmental & Geological Engineering (AREA)
- Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Gas Separation By Absorption (AREA)
- Treating Waste Gases (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261653936P | 2012-05-31 | 2012-05-31 | |
| US61/653,936 | 2012-05-31 | ||
| PCT/US2013/043115 WO2013181252A1 (en) | 2012-05-31 | 2013-05-29 | A method of improving a process for the selective absorption of hydrogen sulfide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2874980A1 true CA2874980A1 (en) | 2013-12-05 |
Family
ID=48577950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2874980 Abandoned CA2874980A1 (en) | 2012-05-31 | 2013-05-29 | A method of improving a process for the selective absorption of hydrogen sulfide |
Country Status (13)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9708196B2 (en) | 2013-02-22 | 2017-07-18 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
| US11440815B2 (en) | 2013-02-22 | 2022-09-13 | Anschutz Exploration Corporation | Method and system for removing hydrogen sulfide from sour oil and sour water |
| US20190115608A1 (en) * | 2016-04-08 | 2019-04-18 | Panasonic Corporation | Electrode, fuel cell and water treatment device |
| US11241652B2 (en) | 2017-05-15 | 2022-02-08 | Basf Se (Reitstötter, Kinzebach & Partner) | Absorbent and process for selectively removing hydrogen sulfide |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3347621A (en) | 1964-11-02 | 1967-10-17 | Shell Oil Co | Method of separating acidic gases from gaseous mixtures |
| US3965244A (en) | 1974-11-27 | 1976-06-22 | Shell Oil Company | Selective removal of sulfur compounds from acid gas mixtures containing significant quantities of carbonyl sulfide |
| US3989811A (en) * | 1975-01-30 | 1976-11-02 | Shell Oil Company | Process for recovering sulfur from fuel gases containing hydrogen sulfide, carbon dioxide, and carbonyl sulfide |
| AU506199B2 (en) | 1975-06-26 | 1979-12-20 | Exxon Research And Engineering Company | Absorbtion of co2 from gaseous feeds |
| US4152353A (en) | 1977-08-29 | 1979-05-01 | The Dow Chemical Company | Method of producing amines from alcohols, aldehydes, ketones and mixtures thereof |
| US4894178A (en) * | 1987-10-13 | 1990-01-16 | Exxon Research And Engineering Company | Absorbent composition containing severely-hindered amine mixture for the absorption of H2 S |
| US4961873A (en) | 1987-10-13 | 1990-10-09 | Exxon Research And Engineering Company | Absorbent composition containing a severely-hindered amine mixture with amine salts and/or aminoacid additives for the absorption of H2 S |
| DE19742911A1 (de) | 1997-09-29 | 1999-04-01 | Basf Ag | Verfahren zur Herstellung von Aminen |
| CN1171659C (zh) * | 2001-09-26 | 2004-10-20 | 南化集团研究院 | 从含二氧化碳的气体混合物中选择性脱除硫化物的溶剂 |
| US7196033B2 (en) | 2001-12-14 | 2007-03-27 | Huntsman Petrochemical Corporation | Advances in amination catalysis |
| CN1219579C (zh) * | 2002-12-11 | 2005-09-21 | 南化集团研究院 | 从气体混合物中脱除硫化物的吸收液 |
| CA2618499C (en) * | 2005-08-09 | 2013-08-20 | Exxonmobil Research And Engineering Company | Alkylamino alkyloxy (alcohol) monoalkyl ether for acid gas scrubbing process |
| JP2014505022A (ja) * | 2010-12-01 | 2014-02-27 | ハンツマン ペトロケミカル エルエルシー | 立体障害型アミン及び関連する方法 |
-
2013
- 2013-05-29 CN CN201380034568.9A patent/CN104619396A/zh active Pending
- 2013-05-29 CA CA 2874980 patent/CA2874980A1/en not_active Abandoned
- 2013-05-29 KR KR20147036343A patent/KR20150044858A/ko not_active Ceased
- 2013-05-29 EA EA201401324A patent/EA027025B1/ru not_active IP Right Cessation
- 2013-05-29 MX MX2014014375A patent/MX2014014375A/es unknown
- 2013-05-29 US US14/402,464 patent/US20150122125A1/en not_active Abandoned
- 2013-05-29 WO PCT/US2013/043115 patent/WO2013181252A1/en active Application Filing
- 2013-05-29 IN IN10231DEN2014 patent/IN2014DN10231A/en unknown
- 2013-05-29 EP EP13727781.0A patent/EP2854993B1/en not_active Not-in-force
- 2013-05-29 BR BR112014029668A patent/BR112014029668A2/pt not_active Application Discontinuation
- 2013-05-29 AU AU2013267524A patent/AU2013267524B2/en not_active Ceased
- 2013-05-29 JP JP2015515153A patent/JP6490579B2/ja not_active Expired - Fee Related
-
2014
- 2014-12-30 CO CO14286802A patent/CO7170138A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA201401324A1 (ru) | 2015-04-30 |
| AU2013267524A1 (en) | 2014-12-11 |
| IN2014DN10231A (enrdf_load_stackoverflow) | 2015-08-07 |
| EA027025B1 (ru) | 2017-06-30 |
| EP2854993A1 (en) | 2015-04-08 |
| AU2013267524B2 (en) | 2015-11-26 |
| BR112014029668A2 (pt) | 2017-12-19 |
| MX2014014375A (es) | 2015-06-23 |
| EP2854993B1 (en) | 2018-12-26 |
| KR20150044858A (ko) | 2015-04-27 |
| JP6490579B2 (ja) | 2019-03-27 |
| WO2013181252A1 (en) | 2013-12-05 |
| JP2015523204A (ja) | 2015-08-13 |
| US20150122125A1 (en) | 2015-05-07 |
| CO7170138A2 (es) | 2015-01-28 |
| CN104619396A (zh) | 2015-05-13 |
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